On this episode of Former Fed Friday, Shelley McGuire sits down with Robert Wood, former Chief Information Security Officer at CMS and founder of Sidekick Security, to discuss what it really takes to secure AI adoption in federal agencies and the companies that support them. Drawing on his experience leading cybersecurity programs in government and advising organizations today, Robert explains why there is no one-size-fits-all approach to AI governance and how organizations can avoid the most common security blind spots.

The conversation explores the difference between traditional compliance and operational AI governance, why understanding your organization’s AI use cases should come before investing in new tools, and how contractors can make smarter cybersecurity investments as AI capabilities continue to evolve. Robert also shares why governance isn’t a one-time exercise, but an ongoing process of adapting to new features, new risks, and new ways AI is being used across the enterprise.

Whether you’re a federal leader, GovCon executive, cybersecurity professional, or AI strategist, this episode offers practical insights for protecting innovation while enabling responsible AI adoption.

To connect with Robert visit him on LinkedIn here.
Learn more about Sidekick Security by visiting their website here.

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